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Hydrochloric Acid → 5-[(6-Chloroquinolin-2-yl)oxy]-2-nitrobenzoic acid

HRID 358124
Notes
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Reaction equation

HRID 358124 reaction equation
[K].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.F[C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([O-:22])=[O:21].Cl>CS(C)=O.O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([O:13][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21])[CH:7]=[CH:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5462222Potassium2×HCID 6931879HCID 6931879, compound2×HCID 178515629HCID 178515629, compound2×

Product 1

HCID 133378695-[(6-Chloroquinolin-2-yl)oxy]-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A reactor is charged with 4.34 grams (0.02 mole) of the potassium salt of 6-chloro-2-hydroxyquinoline (Formula II Compound) in 25 milliliters of dimethylsulfoxide. To this mixture is added 4.46 grams (0.02 mole) of the potassium salt of 5-fluoro-2-nitrobenzoate (Formula III Compound). After stirring at about 100° C. for about 16 hours, the reaction mixture is poured into 200 milliliters of water and acidified with concentrated hydrochloric acid. Filtration and air drying affords 5-(6-chloro-2-quinolinoxy)-2-nitrobenzoic acid (Formula IV Compound).

Workup

  1. filtrationFiltration and air
  2. customdrying

Sources & evidence

ORD record
ord-1bb98feec2e642abb2db4d648a58ece2
Source dataset
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04464533

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes